


Broken Hourglass

by Entangulum_Triangulum



Category: Gravity Falls
Genre: Abusive Relationships, Abusive tyrant, Caravan AU, Cross dressing Dipper, Dipper Protects Mabel, M/M, Mentions of mabcifica, Pirate AU, Prison Escape, abusive, kingdom au, pirate bill
Language: English
Status: In-Progress
Published: 2017-04-22
Updated: 2017-10-05
Packaged: 2018-10-22 09:55:43
Rating: Explicit
Warnings: Rape/Non-Con, Underage
Chapters: 9
Words: 14,710
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10694625
Author URL: https://archiveofourown.org/users/Entangulum_Triangulum/pseuds/Entangulum_Triangulum
Summary: In life, you are destined to one path, just like the sand in an hourglass. But what happens when a simple event strays you from that destined path? This is exactly what Dipper finds out when, in a moment of self-indulgence, accidentally knocks Prince Gideon off of his horse. Accused of treason Dipper agrees to become his wife for two years. However, after only two days at the prince's disposal, he discovers how hideous he is and decides to run away, only to find himself on a pirate ship belonging to the demon of the sea known as "Bill Cipher"





	1. Chapter 1

**Author's Note:**

> So... I'm kind of out of practice for writing fanfiction. I used to write all the time but my last fic was updated... maybe 4 years ago? Anyway, I hope you all enjoy the story I have come up with. I hope to put out updates every two weeks at the most. Thank you for taking the time to read!

Dipper Pines a young man who was a member of a caravan was traveling through a small village with his sister. "Come on DipDop!" The girl shouted for her brother as she ran barefoot through the cobblestone paved streets of the kingdom. Trailing behind her was a young man, much smaller than his sister. He was gasping and wheezing for breath, almost as if he had never run a day in his life. "Mabel!" The boy panted heavily as he tried to keep up with his sister. "Mabel please wait!" He turned a corner in an attempt to catch up to his sister, only to hear a loud crash as he and another person landed in opposite directions. 

The brunette looked up with a hint of defiance, he didn’t do anything wrong so what was the point of apologizing. There on the ground was a young man, slightly taller and fatter than Dipper. Making his small form seem much smaller in comparison. The man groaned as two or three assistants ran over to help him stand up. ‘This guy is so pompous he can’t even be bothered to stand up on his own?’ Dipper thought to himself as he watched the three struggle to get the guy up. 

As they stood the man onto his feet young Dipper Pines decided to take in the details of this man. Just as he thought he was tall and very fat, having multiple chins around his neck. His face, red and contorted, his breathing came out in short yet heavy gasps. It was as if the simple act of standing was much more labor than he was used to. But what stood out the most was probably his hair. Thick and luxurious, it all stayed on top of his head in a perfect mound, barely moving from its place even with the wind howling through the alley. 

Dipper was now getting bored, and he had to find Mabel. The boy attempted to leave, only to be stopped by a set of spears in each direction he went in. “What’s going on?” He asked, having no idea on who he just knocked off their horse. A man walked in front of him, clearing his throat and pulling out a scroll of paper. “You have just committed a crime of treason. By knocking the prince off of his horse you have shown that you are an enemy of the king and all of his assets.” 

Dipper looked around in confusion. Treason? Just for bumping into a guy and just for knocking him off of his horse? How was that his fault? Was it really his fault that the man was so unbalanced that being bumped into by a teenager half his size was enough to knock him off his high horse? Dipper cleared his throat, completely ready to defend himself when he heard a voice. “Dipper!! Dipper!!!” 

He let out a sigh of relief when he heard the almost angelic voice of his older twin. She was great at negotiating these things. Even if she couldn’t get him off scot free, it was possible she could get him off with a much lighter punishment than they appeared to be planning. 

The prince also looked into her direction, intrigued and amazed by the enchantress he saw. A pair of bright eyes, ivory skin, plump pink lips whose color could only be compared with the most beautiful rose in his garden. Oh and of course her hair, thick, silky smooth, and reaching to the back of her calves. An assistant wiped the drool from his chins as he watched the girl run towards the group. 

Thinking of this as a meeting of fate the prince held out his arms, waiting for the beautiful girl to jump into them like in some sort of fairy tale. Only to stand in shock as she ran past him and hugged the boy who had knocked him over. “Dipper bro are you alright?” The prince looked over at them, his face red and contorted with rage. How dare she? How dare she ignore him and dote to the treasonous little brat who had knocked him down a peg. How dare she not realize that he was better. 

The prince was about to make the call for their punishment when he had an idea. He smirked at the thought of it, he knew how he could punish the boy and get what he wanted. “I’ve decided on the perfect punishment for you.” Nothing could go wrong with this plan or at least nothing he could determine. “As punishment one of you two will marry me for a minimum of 2 years.”   
The twins looked towards the prince in shock. Marriage? Who would want to get married to a brat such as this? They looked towards each other, swallowing a bit before looking back towards the man. “It’s actually a great punishment. For two years you two will be separated from each other. One of you will be my bride and will have to perform certain… wifely duties….” He began to pant heavily, his tongue darting out from time to time to slurp away at his chubby lips. “While the other has to live for two years with the knowledge that they might not see the other ever again. After all…. I can be quite… persuasive.”

Dipper and Mabel looked back towards each other, their eyes filled with fear. Both of them were going to be punished for a small mistake Dipper made. One of the guards stomped their spear onto the ground twice, then all of them began to help the prince back up onto his horse. Once he was up he smiled and winked towards Mabel. “I expect you both at the castle tomorrow, and I’m certain you’ll make the best decision on who should stay.” With a loud yell, he and the rest of the guards made their way off, leaving a very confused Mabel, along with a terrified Dipper in the dark alleyway.

 

That night, as their parents fell into a deep slumber the twins were sitting right outside of the covered wagons of their caravan. Completely unsure of what they should do next. “Mabel I saw the way that creep looked at you…. I know he’s expecting you tomorrow.” The girl made a gagging sound in response before shaking her head. “But…. as embarrassing and horrible it will be for me… I know that it’s me who should be going.” 

“Wait for a second Dip Dop, if he’s expecting me to stay, won’t he be mad? What’s stopping him from just hanging you? They considered your bumping into him an act of treason!”

 

Dipper simply shook his head in response to his sisters' worry. His head tilting back as he gazed at the stars. Mabel knew why he was doing this, it was obvious from the shininess over his eyes that he was trying to avoid the tears from streaming down his cheeks. “Mabel… that’s exactly why I should stay…. I’m the one who fucked up by not paying attention to where I was going…. Besides, we’re both 17 now, and we’ll be 18 at the end of the summer.”

 

“But Dipper… that’s just it… we’re going to be 18 at the end of the summer… that will be the last birthday we can celebrate together.”   
“Mabel…. If I don’t go… then I’ll put our entire caravan in danger. I’ve made up my mind…. I’m staying at the palace as that little creeps… ugh… wife..”

 

The next morning Dipper and Mabel met each other at the crack of dawn. From the redness in his sister's eyes and the bags beneath his, it was obvious that neither twin had gotten much sleep. Mabel looked towards the bundle that was slung over her younger brother's shoulder and immediately wanted to cry again. 

“So Dipper… are you ready to go?”

Dipper was silent, only nodding as he began to trudge his way into the city and towards the palace. Even if he didn’t feel like speaking he wanted to take his time. After all, this would be the very last he would ever see his sister.

The twins continued to walk, Mabel making comments on how it was a nice day out today. Dipper only nodded in response, breathing heavily through his nose as he tried to keep the tears from rolling down his cheeks. This would be the last time he would hear his sister’s voice. They continued to walk, Mabel did everything she could to cheer up her little brother. She bought a flower which she quickly put into the boy’s pocket. She also stopped at a small bakery and bought Dipper his favorite pastry. She even tried to buy him one of the thickest books at the bookstore.   
Although each gift was accepted with a nod of gratitude Dipper Pines still didn’t say a word. He was certain that the moment he would try to speak he would immediately break down, and cause his sister to take him back home. Thus the twins continued to walk in silence. Purposely taking side streets, stopping to look in every store window that they could find. Stopping to pet every animal that would let them. They simply wanted to milk every last moment they had together.

Unfortunately, it was not to last. Eventually, as the sun reached its highest point, the twins appeared at the stairway to the castle. They glanced towards each other as if they wanted to say something. Then looked back towards the flight of steps in front of them. 

Dipper and Mabel began their ascent. Both of them slowly pulling their way up the stairs. The guards began to move aside. However, Dipper and Mabel did not notice, as they would only look at each other or the ground beneath them. One step at a time, it seemed as if the stairs were much larger than they appeared. The two looked straight ahead when their gaze met the ironclad boots of the guards.

One of the guards cleared their throats as they looked to the twins. “Only one of you may enter.” Dipper quickly looked back to his sister, before hugging her as tightly as he could. They stood still for a few minutes, holding each other tighter and tighter. Eventually, they pulled away from each other. The boy couldn’t help but to notice Mabel’s face, wet with tears, bangs a mess, and a bit of mucus dripping from her nose. 

The girl pulled out a small handkerchief, blowing her nose into it and stuffing it back into her blouse pocket. “Dipper… please be careful…” She then glared to the guard and stuck her finger in his chest. “If I find out that anything bad has happened to my little brother I will not hesitate to call a war upon this country, and I will overthrow your kingdom.” It was an empty threat, there was nothing she could do once Dipper entered those doors. The boy stood in the doorway, watching his sister descend down the stairs, and into the city. Where she disappeared, blending into a large group of people.

Once she was gone, one of the guards quickly took Dipper’s hand and lead him into the castle. “The prince won’t be happy with this… he was really looking forward to the girl coming in.”

“Why should she take the full brunt of the punishment? I’m the one who screwed up.”  
“Prince Gideon would have treated your sister very well, I’ve never seen the boy so infatuated with anyone.”

Dipper could only shake his head as he carried the bag over his shoulder. He followed the guard through multiple hallways and corridors. Through rooms, and courtyards. It was strange how many twists and turns it took just to get to where they were going. However, the two eventually reached a large marble door. “Good luck in there… you’re going to need it.” The guard quickly walked away, leaving Dipper alone with the door, and whatever was beyond it.

The brunette stood in front of the marble doors. Trembling horribly as he took a few deep breaths of sweet, sweet oxygen, then gave two quiet knocks. “Come in~” The overly joy filled voice of the prince rang in his ears, it was obvious that he wasn’t expecting the boy. With a sigh he entered the room, only to be greeted by the large, chubby man sprawled in nothing but his thin, silk undergarments. 

Gideon, however, was just about as happy to see Dipper, as Dipper was to see him in the nude. “What are you doing here!” His shrill voice filled the room as he quickly jumped up, his excess fat rippling and swaying about as he jumped up and ran over to Dipper. “I do not enjoy jokes, especially from traitors!”

Dipper glared at the prince, growling as he tried to make himself seem bigger. “She should not be punished for my mistake. I am here swallowing my pride and taking the punishment in order to protect her. So you better get used to having me a-” A loud crack filled the room as Dipper fell back onto the floor, a stinging sensation filling his cheeks as he looked up to the prince. Gideon’s face was dark red with fury, his hand clenched tightly into a fist as he struck Dipper once again. The red spot on his cheek turning a dark purple color. “How dare you defy me! I wanted your sister!” He stopped and smiled at how Dipper cowered beneath him, an idea forming in his mind. “And that is exactly who you’ll become.”

 

3 days passed since Dipper had entered the castle, the brunette stood in the middle of the prince’s room, wearing nothing more than a set of soft robes. Gideon walked into the room and glared at Dipper. “Why is your outfit incomplete?” The man walked over to Dipper and grabbed him by the front of his clothing. “Put the wig on or I’ll force it down your throat again.” The prince snarled as he shoved Dipper into the frame of his bed. The force of impact causing the boy’s face to be cut open. “I will be back in 10 minutes! You had better put that wig on and be prepared to offer yourself to me by the time I get back!”

Dipper watched the prince leave before falling to the ground, tears rolling down his cheeks and burning the wound on his face. He hated this, he couldn’t spend another moment in this place. He decided that he would leave, and without another thought, he threw the wig onto his head, gathered his things, and climbed out of the window.


	2. Chapter 2

**Summary for the Chapter:**

> Dipper Pines makes a few new allies and meets a long-lost member of his family. Gideon becomes obsessed with Dipper's capture as the law states that nobody else can take his punishment now that he is in the records.

**Notes for the Chapter:**

> So I'm going to try and get a bit more writing practice in today (because that's why I'm writing this fic). Dipper is going to be wearing the wig for a few more chapters.

Dipper let out a soft series of short gasps as he ran into a building, ducking just below the window as the guards stomped past. "Find him! Find the traitor!!" He shut his eyes tightly and whimpered until the rumbling stopped. The young man stood up and looked out the window, sighing in relief as the mob disappeared. He was safe, for now. "So what did you do to get the prince this pissed off?" He jumped up and turned himself around, standing behind him was a tall woman with thick red hair. A smug smile spread across her face as she crossed her arms across her chest. "Oh, man are you okay?" Her smug grin turned into a look of concern as she took Dipper's chin in her hand and turned his head. "That's one deep cut there Sis... Yo Soos! Bring me some bandages and the anti-biotic ointment!!"

Sis? Dipper looked confused as he ran a hand through his hair, then let out a shocked gasp. His hair, the wig, he was still wearing that horrible wig that little monster was planning to subdue him in. "I... wait I think you're confused I'm-" He was cut off by the sight of a large man, somewhat resembling a hairless rodent coming over with a roll of gauze. "Okay dudes! I got them!" The red headed woman let out an irritated sigh and took the antibiotic from him. "Soos, I said bring the bandages. We're dressing a wound. NOT wrapping up a mummy!"

Soos, as he was called looked at the bandages in his hand and then towards Dipper with a frown. "Ah I'm really sorry Wendy, but these are the only bandages that Mr. Pines will buy." Dipper looked at the two, mouthing out their names a few times in order to help himself remember them. "Alright Soos, go to my pack, there is an old t-shirt and some honey in there, bring those to me." The large man gave a nod and ran into the back of the building. Wendy turned to Dipper with a smile and proceeded to clean the wound. "I'm sorry about him, he's a good guy, real nice, but sometimes he's not exactly... all there. So tell me about yourself, what's your name?"

Dipper became shocked as he was addressed in such a casual manner. His name? He didn't know what to say. If he told her the truth, he might be ridiculed for dressing like a girl, but if he lied he might be discovered and called disgusting. The boy looked around, desperate for an answer and then with his head hanging low decided to simply state the truth. "I... I'm not a girl... My name is Mason Pines... and the reason I'm wearing this wig is... because I'm running away from that fat pig known as Prince Gideon." He braced himself, waiting for the woman to call him disgusting, waiting for her to throw him out and hand him over to the royal guards. Instead, he heard a small laugh. Followed by a loud cackling. "Oh man! Dude I knew you were a boy the entire time!! I just didn't want to throw you off like that!" The redhead wiped a tear from her eye and sighed before kneeling down to Dipper's level. "I'm impressed you lasted as long as you did, there was a town crier in the city the other day talking about what happened with you. I've seen potential wives jump into the ocean just to get away from him after a few hours. You're a pretty tough kid to be able to deal with someone like him."

She playfully punched Dipper in the shoulder just as Soos came back with an elderly man. Dipper looked up at him and turned his head to the side. Sometime, somewhere before he had seen him. But he just couldn't figure out where. Wendy grinned and stood up, motioning for Dipper to do the same. "Guys this is Mason Pines, he's in disguise and needs our help to escape from Prince Fatty." She smiled and held the boy's arm up, earning a short cheer from Soos and a cough from the elderly man. "Let me get a look at you, my boy." Dipper turned to see the man, his head adorned with thick gray hairs, glasses squared off around the edges, his red jacket embroidered with an orange fish over the breast pocket. He tilted Dipper's chin up with his cane, smiling as he reached upward and smoothed Dipper's hair back. Revealing his constellation shaped birthmark. "I don't believe it, it really is you. I haven't seen you or the rest of the family since the day you were born."

Dipper was confused, who exactly was this man and why was he acting so familiar with him. "Ah I don't expect you to remember me, but I do want you to know that we are related. I'm your Great Uncle Stan. But you can just call me Grunkle Stan!"

His great uncle. In such a hellish time in his life, the young man never expected to be graced with the chance of meeting his long lost Great Uncle. He didn't even care that he didn't have the time to really enjoy the moment. He knew immediately that when he heard the word 'family' he could trust these three people. "Hmmm now let me think if there's one thing I know it's how to avoid being arrested. Wendy, get to dressing his wound." The red head gave a nod, took the items from Soos, and proceeded to begin her work on the large gash on Dipper's cheek.

"What should I do Mr. Pines?" Stan gave a thoughtful look and began to look around, almost as if he were trying to find him something to do. "Go to that fancy pants shop and get Dipper here some actual clothes, the robe he's wearing is a dead give away. How about one dress and a pair of pants and a shirt?" Dipper wanted to complain about the dress, however, Wendy wouldn't let him move as she smeared the honey into his wound. "So Mr. Pines, why did you have Soos go get a dress."

"The answer is simple. Pity. Men are more likely to take pity on and help a distressed young woman than they are with a young man. With that wig, a bit of makeup, and the dress he'll be set to sneak aboard one of those ships. Once they're out in open waters, then he'll be free from their tyranny." The elder man smirked, obviously proud of his own idea. Dipper wanted to complain about the dress, however, after hearing the explanation to that piece of the plan he couldn't help but keep his mouth shut. His great uncle really was looking out for him after all. 

Just as Wendy had finished dressing the wound on Dipper's cheek, Soos came in, panting heavily as he held out the bag of clothing to them. "This was the best I could do dudes! They wouldn't let me have anything else because I didn't have much money."

"It's fine Soos!" The old man's gravelly voice filled the room as he reached over and took the bag. "These will work just fine, he's escaping not being part of a fashion show. Wendy, take Mason upstairs and dress him up. I assume that you have a corset that he can borrow, considering you went through 4 sizes in the past two years"

"Alright, Mr. Pines I get it! Come on Mason, let's get you upstairs."

Dipper followed Wendy up the steps with a discontented sigh. He hated his real name, it sounded unmanly and almost girlish to him. Almost as if his parents decided that his name would sound better if it were a close copy of his sisters. "Dipper." He finally managed to choke out, his nervousness from the bizarre situation finally subsiding. "What was that?" Wendy inquired as she looked back at him with a smile. "Dipper... I prefer to be called Dipper.... It's because of my birthmark."

"Okay man, Dipper it is.. now take off that robe and step over here. " Dipper did as he was told, his face flushing a soft pink as he revealed the multiple bruises he had accumulated over the past few days to the woman. "Hey man, don't worry. I'm not going to judge you or anything like that. Now grip the chair so that I can get this corset on you. This is the only hard part, the rest will be easy."

Despite how he would never admit it out loud Dipper actually had some experience wearing a corset before. His sister would from time to time use Dipper as a mannequin, as he was the only other person in the group who shared a similar size with her. He could feel the laces being pulled and woven in the back, then a mighty pull, effectively encasing his rib cage and rearranging his insides. "I can hardly breathe..." The boy wheezed out as Wendy finished tying the corset. "That's how you're supposed to feel. If you're having an easy time breathing then it's been tied up wrong." She clapped her hands and handed him the dress, a fluffy full-skirted white topped and dark blue bottomed party style dress. On the left breast was the simple embroidery of a pine tree, dark blue just like the skirt of the dress. 

Wendy stood back and whistled. "I think I could totally pass you off as my little sister or something. We just need to put a little bit of makeup on you." She smiled and pulled out her compact. "Now just hold still. This is just to make you look more like a girl." She began to work, thanking the fact that she didn't need to work too much as Dipper was already fairly feminine. "A bit of blush and some eyeliner... now close your eyes I have some lashes to put on you... There, finished!" She stepped back, obviously proud of her word. "Okay, now I'm almost done. I just need to see if I managed to save an old pair of my shoes." She headed towards the closet as Dipper looked into the mirror. 

In the mirror, he could have sworn that he saw his sister Mabel. Except he didn't look like Mabel as well. He looked as if someone had painted his sister and put her up for the world to see. "Wendy... why do you live here? Are you a Pines as well?"

Wendy poked her head out from the closet and shook her head. "No man! I'm living here because I didn't want to join my dad and brothers in the mountains. Not when I have great friends and a decent job here."

"Don't you miss them?"  
"Yeah I miss them, but so what? Besides they always stay in the city during the fall and winter months because the weather gets so bad up there... AHAH! I found them!"

Dipper suddenly jumped as two pairs of shoes were thrown at him. A pair of black mary janes, and a pair of white kitten heels. "Those are probably the only shoes I have that might fit you. You have pretty small feet." She smiled and handed him a pair of stockings as well. "I think the mary janes might be easier for traveling so I would wear those and put the other ones in the bag we're packing up for you."

"You guys are packing a bag for me?" Dipper looked up to Wendy, an obviously grateful smile spreading across his face. "Of course we are! We can't let you go off into the world unprepared. Besides what kind of big sister would I be if I let a kid like you go off with nothing but a slap on the back?" The brunette immediately hugged the woman, who happily returned the gesture. "Now get those shoes and stockings on, Soos will be escorting you to your next destination soon."

Soon Dipper was ready and he was lead down the stairs by Wendy, who presented him with an imitation of a Trumpet. "Presenting! Maryanne Pines!" She stood back and gave a few faux cheers as Dipper came down the stairs. His long, unkempt wig now neatly trimmed and braided in order to finish the look that the dress gave him. Soos gave a cheer and looked over to Stan who gave a short grunt. The elder man walked over and looked at Dipper as if trying to figure out one last piece he needed. "I know what's missing! Soos go get my old glasses, and make sure to pop the lenses out of them!" Soos gave a quick salute and ran out, returning almost as quickly as he left with a pair of round frames which Stan promptly placed on the boys face. "Perfect. Now nobody will recognize him." He stated proudly before pulling the teen into a tight hug. "I hate this... I haven't seen you kids for almost 18 years and then.. finally... I get to see one of you and it's under circumstances like these... can you do me two favors kid?"

"Anything for you Grunkle Stan."

"I want you to try and find my brother, Stanford Pines... he went out to sea years ago and never returned... but I know he's still alive. If you find him just tell him that you're his grand nephew and I'm sure that he'll be able to help you if you need it."

"Okay... I can do that." Dipper could feel the tears stinging his eyes as he tried to fight them back. "What's the other favor?"

"I want you to write to me whenever possible, but don't sign your name on the cards. Use something like a Pine Tree as a symbol... that way I know that it's from you."

"I'll do that.. thank you so much, Grunkle Stan... You're the best." The boy hugged his Great Uncle one last time before being lead away by Soos. He gave a short wave as he went out the door and the two began to head towards the docks. 

O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O

Back at the castle, Prince Gideon was growing more and more furious. "WHAT DO YOU MEAN YOU CAN'T FIND HIM!?" He shrieked at his father, King Buck, before throwing a piece of expensive china and smashing it against the wall. "Now Son I..." Another piece of china shattered against the wall behind him. "I own you old man! You would not even be king if I weren't here! Now tell me why you can't find HIM!!"

"Now son look we have every officer and guard in the city looking for that boy, and besides I thought you didn't even like him!"

"It doesn't matter if I like him or not! That boy humiliated me, and I'm determined to see him humiliated as well. This isn't about like or dislike. This is about vengeance. He humiliated me by knocking me off of my horse... he humiliated me a second time by coming here instead of his beautiful enchantress of a sister.... AND I'LL BE DAMNED IF I LET HIM HUMILIATE ME BY RUNNING AWAY! NOW GET TO FINDING HIM!!!"

Without another word the king left, apologizing profusely to his son. "Lock down the city, only those with permits may be allowed to leave. We cannot risk upsetting my son anymore."

**Notes for the Chapter:**

> Oh wow, that was a lot of writing... I hope I did okay with the character portrayal and what not. That has never been one of my strong suits. For those who are wondering, Bill is going to be coming in the next chapter and things are going to start getting really interesting. Thanks again for reading!


	3. Chapter 3

As he walked outside Dipper flinched as he felt Soos wrap an arm around his shoulder. "Sorry dude, in this city female citizens have to have somebody escorting them like this... it's not a law but a lot of stuff can happen to a girl who walks on her own." Dipper looked down and frowned at the thought of his sister, who left the castle on her own. Of course, she was tough as nails, and her love of sweets filled her with energy that could only be compared to that of a shooting star. Of course, that was how he felt about the girl. 

The two continued to walk, speaking about the newly discovered constellations and other things. It felt nice to have another person share so much of his interests, even if he would only be able to speak to him for small amounts of time. Eventually, the pair reached the docks, Soos let out a sigh of relief as he began to hand Dipper his bags. As the younger male began to situate himself a pair of guards walked over, a short, fat one with black skin and a thick mustache, and a tall, thin, white one with very little hair. Both of them walked up to Soos and Dipper as the skinny one cleared his throat. "Excuse me you guys, we've been ordered by Prince Gideon to find his bride to be. The prince is deeply worried about her well being and would like her to return as quickly as possible."

Dipper let out a soft whine, barely audible to anyone except for himself. He knew perfectly well why Gideon wanted him back, he knew what the prince was really like. However, it seemed apparent that the people living in the city didn't seem to realize how horrible he truly was. As he had walked through town he couldn't help but notice all of the strange caricatures of the prince, illustrating him as a magnificent being who was to be loved, and whose very presence needed to be celebrated at all times. Soos recognizing Dipper's obvious discomfort decided to take the wheel, despite being shy spoken, and unsociable himself he knew that as the older person it was up to him to speak to the others.

"Sorry dudes but we haven't seen her. Are there any photographs of her that we could use?"

"Photographs?" The fat one looked to the other with a frown. "Durland and I were just ordered to go find her. We weren't given any type of description to follow, let alone a picture." Dipper immediately relaxed at the other's statement, they didn't know who they were looking for at all. "Chief Blub's and I are from a couple of towns over, and all we were told was that there would be a large reward for finding the missing princess. " The two looked towards each other in disappointment as they began to think of other places to search. "It sounds to me like... he doesn't really want to find the princess...." Dipper knew this was a lie, and that the other was searching for him in a manner that could rival the hunting tactics of a cougar. However, if he could get these two off of his trail, perhaps others would follow. "If they really wanted to find her than they would have ensured that everyone knew who they were looking for right?"

Blubs and Durland gave each other a thoughtful look then looked down with a defeated look on their faces. "What should we do Chief? We really needed that money." Dipper couldn't help but feel bad for the others as he began to look around, desperate for a solution to their problems. "I know... we could have rebuilt the station... but I guess that won't happen now..."

"I wouldn't give up hope that easily.... haven't you noticed that the capital is swimming with elites? Perhaps if you really thought of something you could find a way to raise the money that you need to." Blubs and Durland gave each other a thoughtful look, before shouting in unison. "CRAB FISHING!!" With that, the two waved goodbye to Dipper and Soos and merrily went on their way. Dipper couldn't help but fall to the ground as a sigh of relief escaped from his body. "Oh my god... I can't believe that we managed to pull that off..." 

Soos gave a shocked look before nodding in agreement. "Dude that was incredible! Where did you learn how to do something like that? Law enforcements aren't exactly easy to trick." He handed Dipper his bag with a smile and patted the boys shoulder. "This is where we have to part ways little dude, are you going to be alright?"

Dipper grinned and adjusted the glasses on his face. "I'm certain that anywhere I end up, it will be better than having to spend the next to years as prince fat-ass's wife." The took shook hands, and pulled each other into a tight hug, before Dipper ran towards the docks as he heard his dear friend call out to him "Good luck!"

Dipper began to wander around the ships, trying his best to find one that was large enough for him to sneak onto. Unfortunately most of them were of modest size, if he were to sneak aboard he would be discovered in an instant. 

However he had to keep trying, if he didn't the efforts of his new friends and rediscovered family would be in vain. Dipper kept walking along the long docks, searching for a ship just large and crowded enough that he could go unnoticed. 

Finally, just as he had stopped to pull off the mary janes he was wearing, he spotted it. A large vessel with a wide assortment of men and women loading themselves aboard. Surely, he could easily blend in with such a large crowd. With a small smiled on his face he threw his bag over his shoulder and slowly walked towards the crowd. Weaving himself in between the people climbing aboard. He nervously shimmied down the narrow gang plank and let out a sigh of relief as he fell against the side of the ship.�  
"Now what do you suppose you're doing here darling?"

**Notes for the Chapter:**

> I apologize for the chapter being so short this time around. My keyboard has been acting up and I haven't had much time to write this past couple of weeks. (also the plot for this chapter was rather bland, but hey not all chapters can be angst filled excitement)
> 
> While I like to take the time to thank everyone for their support personally I would like to thank everyone for their wonderful comments and anyone who has given kudos to this work. It's your support that keeps me writing.


	4. Chapter 4

*Warning. This chapter contains a nonconsensual sexual situation. Please read at your own risk*

"Now what are you doing down there darling?"

Dipper looked up almost immediately, he thought that he had hidden perfectly and now he had the entire ship staring at him. "Well? Are you going to speak? Or do I need to spark some flames into you?" The woman held a hand to her mouth and laughed her pink hair bouncing on her head with each movement of her body. "Hmmm now, what shall we do with you?" She put a finger to her mouth and began to think. "We could work you like a dog, but I feel as though that's too light of a punishment for someone who has the guts to sneak aboard this ship... we could feed you to the sharks once we're out on the ocean... or we can tie you up and let all of the men on the ship have a turn with you."

Dipper was shaking like a leaf, he didn't understand or like what was going on, and he knew that he would be in trouble if he didn't think of something soon. "Teeth! 8-ball! What do you think?" Dipper watched as two men walked towards him, one who grinned from ear to ear, showing off all of his pearly whites to the world. His head shaved bald and short stature seemed to contrast with the large jaw he had. The other man had reddish brown hair which stuck upward in a manner like horns, on one eye was a patch with the number 8 written on it. They both stared at Dipper, grinning widely as they began to examine him. "Hmmm... she's pretty cute, and with eyes like those you know that she would submit easily." Teeth stated as he leaned in close to the boys face, the smell of rotting fish permeating from the man's mouth. 

Dipper let out a whine as he tried to pull himself away from the other. Tears rolling down his cheeks as his mind began to race. 'I'm going to be killed.... I'm going to be raped... I'm going to be raped and killed.....' At that point, 8-ball cleared his throat and looked to the crew around them. "May I remind you all that while torturing the girl might be fun, it is Captain Cipher who makes the final decisions around here."

"Did somebody say my name?" The entire crew immediately shifted their attention to a man who was walking towards them. He was tall, about 6 feet from what Dipper could guess. His skin tanned to the point of being a deep brown color, his blonde hair shining as though it were made of gold. He walked towards Dipper, wearing copious amounts of gold which covered the bare skin of a naked chest. His pants held up by a large piece of rope, and of course, the cape on his back flowing in the wind as he reached up and held his hat on his head. He looked at Dipper, analyzing the boy as if he were assessing him like a piece of produce from the market.

"You've got guts kid." Dipper flinched at the sound of his voice, which sounded akin to the sound of a nail across a slate of some sort. "But you are dressed pretty ridiculously, take that crap off." The brunette sat still and stared for a minute, not processing what the man had meant by that. "I... said... take it off!!" Bill reached down and grabbed the glasses and wig, ripping them from the boys head and face before tossing them into the ocean. The entire crew stared at Dipper, openly mocking him for how he looked. Bill continued to stare at Dipper just as the crew began to shout for them to throw him overboard.

"Hold it!" The captain stood up with a grin, tapping his chin thoughtfully as though he were trying to figure something out. With a snap of his fingers, he pointed to Dipper with a smile. "You're that 'princess' who ran away from Gideon!" He grabbed Dipper and pulled on his arm in order to make him stand up. "What do you say, boys? Should we give him back to that kid?" Dipper listened as the crew shouted angrily, one of them pulling out their sword and swinging it around. "Well it's unanimous, the kid stays here." Bill gripped Dippers arm and pulled on him, his grin spreading from ear to ear as he escorted the boy towards his cabin.

Once inside the younger man turned towards Bill, his mouth just barely opened to say something before the man's hand struck him hard across the face. Dipper let out a soft grunt as he found himself on the others bed, his heart pounding heavily as he stared at the pirate captain. Who's face was still filled with a strange giddiness. As if he were a hunter, sadistically playing with its prey. "You really are stupid, aren't you kid?" He didn't even give Dipper a chance to respond before striking him once again. "I make the rules on this ship, and I decide what happens to everyone who comes on here. Most kids like you, I wouldn't have even thought twice about throwing you to the sharks, but today I felt nice and decided to let you live." He took Dipper's chin in his hand, smiling down at the boy as he licked some of the tears from his cheek. 

"Now don't cry? You're not really scared of me, are you? After all, I could just give you back to Gideon? But you like it better with me right?" Dipper gave a shaky nod to the question, which Bill seemed to be pleased with. "Wonderful, now here is your position. Around the ship you will be referred to as the cabin boy, meaning that while we're in the company of others that will be your title. In here I will call you as I damn well please and you may only refer to me as captain or master. Do you understand?" 

"Yes.... captain?" Bill smiled approvingly at the boy before giving a nod. "Good boy, you don't want to have to go back to Gideon now do you?" 

"No, captain."  
"Perfect, you're already catching on so quickly, I will on occasion tell you what I want to be called and I expect you to be able to comply with my demands. Another thing is that you must do what I say when I say it or else there will be consequences."  
"What kind of consequences... captain?"

Dipper was already terrified, he didn't know what to do therefore he just did as he was told, hoping that he would be able to leave this place unscathed. "If you do not comply with my demands the punishments will go in this order. The first time you fail will result in physical pain, varying on your level of insubordination. The second time, I will ensure your public humiliation in front of all persons on this ship. If you fail a third time I will bind and gag you as each man on this ship has a turn with you."

Dipper didn't know what to do, he thought he had escaped hell when he stepped onto the ship. However, it seemed that satan himself had greeted him. "Now, do you understand the rules? Or do I have to repeat myself?" He shook his head, his heart pounding wildly as Bill leaned in close, his single eye boring into his. "Good boy." The blonde pirate ran a hand through his curly brown locks before climbing off of him. "Hmm, I like the choice of clothes Pine Tree, especially what's underneath." Dipper looked down, seeing the skirt of the flipped upward, revealing the feminine undergarments he had on. "I... This is...." He tried to close his legs and fix the skirt, only to have Bill stop him.

"Hold still." The pirate smirked as he placed his face in between the boys' thighs. Mumbling softly as he nestled his face into his private areas. Dipper wanted to shut his legs, however, Bill managed to hold him down and continue his work. A soft whimper escaped from the boy's throat as he felt the other nibble on his growing erection, a dark blush growing on his face.

Bill pulled away with a smirk, licking his lips as he looked at Dipper. "Very nice, I look forward to doing that again Pine Tree." He sat back down at his desk and leaned against his chair. "Now are you going to lay there like a dumb ass, or are you going to get started on the chores? The deck needs swabbing so move it Pine Tree!" 

Dipper laid back on the bed, his face a dark red as he tried to process what was going on. Before finally getting up and running outside just as the blonde began to growl at him. As he ran to the upper decks, he looked towards the capital city as they drifted away from it. "I guess.... I'm stuck here..." With that he picked up the mop that had been left for him and began to clean the decks.

**Notes for the Chapter:**

> I'm not a really big fan of this chapter, but I kind of wanted to set up the four main characters on the ship. (besides Dipper obviously)
> 
> So here are a few details about the crew that I didn't feel like mentioning.
> 
> Bill's crew has a total of 77 men. Including Dipper and Himself.
> 
> Most of them do generic work, however, there are some jobs that are given to specific people.
> 
> Pyronica is the navigator. She keeps the ship on course and ensures that they get where they need to be.
> 
> Teeth is the chef, he makes the food and decides what everyone eats.
> 
> 8-ball is one of the shipwrights. He keeps the ship running and does repairs.
> 
>  
> 
> I think one of my own biggest issues with this chapter was having Bill tease/molest Dipper like he did. However, I wanted to put it in his character that he does what he wants to do because he feels as though he can.


	5. Chapter 5

The gentle rolling of the waves rocked the boat at sea. The swaying back and forth was something that any average seafaring man would be used to by now. Unfortunately, this was not the case for young Dipper Pines. 

Of course, not wanting to go easy on the new kid, the rest of the crew decided to take entertainment by watching him be miserable instead of actually helping him. Dipper moaned softly as he hobbled over to a pole and grabbed onto it. His mouth opening in a gasping motion as his head began to spin. Copious amounts of drool dripping from his mouth as he tried to hold back the contents of his stomach.

Nausea from the sea sickness, along with the heat from the summer sun seemed to make the whole situation even more unbearable. His vision completely unfocused, and the voices of those making fun of him warping into what sounded like some sort of demonic entity. 

At this rate, Dipper knew that he was either going to throw up or pass out. He just wasn't sure what he would prefer. As his vision began to fade out he could just barely see the silhouette of a tall man with large hands reach out for him.

O.O.O

Dipper woke up in a small bed with a soft groan. His stomach feeling like it was starting to settle, as well as the cold pack on his forehead reducing his fevering state. He wanted to try and sit up, however, all he could do was simply lay back in the bed. 

He took a moment to look around the room in order to try and assess his situation. On one wall was a shelf full of books, most of them appearing to be medical dictionaries. Along with them were items such as bandages, medications, and ointments as well as many other things. He was in the ship's medic office. �  
He glanced over to the other side of the room and stared at the man who sat at his desk. He was an older man, probably the same age as his Grunkle Stan. His gray hairs somewhat thick and youthful in appearance was a contrast to his aged skin. Dipper watched as he appeared to write in a small booklet, barely noticing that the other also had something weird about him. 

However, one can only watch or examine for so long. Yet while Dipper liked being to lay down, he knew that if he didn't finish his chores soon he would be in trouble with the captain. "Excuse me?" His voice came out in a hushed whisper, which was just enough to startle the other.

The older man quickly turned around before letting out a sigh of relief. "Oh hey, you're finally awake." He let out a laugh as he reached over and pulled the cold pack from his head. "That's a relief, Bill was just threatening to come down here and as he said 'fix you himself'.... ungh.... Anyways how are you feeling? I don't think I ever saw anybody who had seasickness as bad as you did."

He began to examine the boy, shining lights into his eyes, mouth, and ears just before he could answer the question. "I think I'm doing ok.... Mr?"

"My name is Stanford Pines."

Upon hearing that name Dipper grew excited. It was as if any sign of illness he had was now gone. Pines, that name just kept on swimming through his head. "You're also a Pines? My name is Dipper Pines."

Stanford didn't seem to be as excited by the name, however, the name Pines was fairly common. He began to think of ways he could try and trigger some form of reaction from him. "Oh! Do you know anybody of the name Stanley Pines? He's my great-uncle and-"

"Did you say..... Stanley Pines?"  
"Yes. I did say, Stanley Pines."  
"And did you say he was your Uncle?"  
"Yes, that is right."  
"I can't believe this..."

Stanford let out a soft laugh as he rubbed his eyes with his fingers. "I...I have a nephew.... After being trapped on this ship for the past 30 years I find out that I have a nephew and he's sitting right next to me."

Dipper had never expected this type of reaction. He could feel the joy rolling off of the elderly man in waves as he was pulled into a tight hug. "I have a nephew. I have a family member right here on this hell hole of a ship!" He pulled away from the hug, staring at Dipper for a moment before running a hand through his curly brown locks. "You have a birth anomaly as well Dipper."

He smiled as he brushed his hand against the boy's forehead. The constellation shaped birthmark seeming to put him in a trance. "Well, Dipper if you ever need anything please don't hesitate to ask. I made a mistake long ago by running away from my family. But I refuse to make that mistake again. You ever need anything at all you just come down here."

He patted Dipper on the back with a smile. "Also Dipper.... I think it would be best to keep our being family a secret. Bill doesn't like to allow those types of luxuries to us. He thinks that if there are family members aboard, then they might start a revolt."

"I understand sir, thank you for letting me know." Dipper sat on the bed, staring at the man who was his great Uncle. He couldn't believe how similar the two of them looked. of course, being family and twins it shouldn't be that surprising. He wanted to enjoy some more time with his uncle, he really did. However, that was not to happen. 

Bill seemed to have the tendency to enter in a way that gained attention from everyone around him. He would announce his presence, slam doors open. Whatever he could to ensure that all eyes were on him. "Well well well.... I see that my little servant has been making himself rather comfortable instead of doing the chores he was given... Hmmm." The blonde smirked as he gripped the younger man's chin, forcing him to look at him. "I wonder exactly how I should punish you for not obeying my orders?" 

Stanford cleared his throat and placed his arms over his chest. "Dipper is in here because he is currently not well. A mixture of seasickness, heat stroke, and of course dehydration. Remember Bill, we have a deal that what happens to my patients while they are in my care is my business. Dipper will not be punished for the time he spent in here today and I expect you to give him the time he needs to fully recover. 36 hours ought to cover the time he needs." 

Bill's face contorted with irritation. He hated to be told what he could and could not do. However the fact that they made a deal was true, and although he was a liar and a cheat, he always complied with any deal he made. Even if he used more underhanded methods to sneak away from it. "So for the next 36 hours, Dipper cannot do chores?"

"That is correct."  
"And it would be best if he stayed in bed?"  
"Yes, that would be ideal."

"Interesting." Bill grinned from ear to ear as he figured out a small hole in Ford's demands. Perhaps he would be able to have fun with the kid after all?

Dipper watched the grin spread on Bill's face, watching that look of anger become one that resembled some sort of hungry animal. His heart began to beat wildly as he tried to think of a way to get himself out of this mess. However, before he had a chance to even speak the captain picked him up, and slung him over his shoulder with a grin. "Now then, shall we head back Pine Tree?"

Dipper knew that he didn't have to answer that question, as for whether he liked it or not Bill would simply do as he pleased and drag him down to his cabin no matter what he said or did. He rested his chin on the man's barely clothed shoulder which was just covered by his cape. Giving the boy's face some protection from the heavy gold, and platinum that he had adorned all over his body. Necklaces, chains, rings, earrings. That and his golden colored hair, one could look at Captain Bill Cipher and think that he was the living embodiment of a treasure chest. 

The walk to the room was short, however, it did not make it any less embarrassing. As he was almost an adult, Dipper had a hard time adjusting to the fact that he was being carried like some little kid. Of course, the crew members made things worse, some of them outright pointing and laughing at him. Others taking the time to make lewd hand gestures towards Dipper. He hated this.

Bill threw Dipper onto the bed, watching as the boy bounced a bit before he let out a pained mewl. The pirate captain walked around the bed, observing Dipper as if he were a small animal on display. A dark blush filled the younger man's cheeks as he placed a hand over his mouth. Bill grinned from ear to ear, his teeth, unlike many others on the ship were bright and shiny. That along with the toned muscles that were distributed throughout his body. It wasn't hard to admit that the man looked good. "Oh this is going to be fun, isn't that right Pine Slut?"

He began to crawl on top of Dipper, holding the boy down in order to give him a kiss. Of course, in a moment of good fortune as Dipper would call it, the door slammed open, revealing a panicked 8-ball on the other side. "Captain Cipher! We're heading into a storm! There's no way around it and we need you on the upper decks!"

Bill, obviously irritated, let out a long sigh before climbing off of Dipper and walking out to the deck of the ship. "You be good Pine Tree." He grinned as though he were saying goodbye to a beloved family pet, before slamming the door to his cabin shut.

**Notes for the Chapter:**

> Alright! I think this has been one of the better chapters I have produced in weeks. It's hard to keep up a plot but I'm trying my best. Also, I enjoy constructive criticism, everybody! I am using this fic as a way to practice my writing and improve myself. However, I can't improve if I am not given points to improve myself on. Anyways thank you all for staying through, even with the bad chapters I had come up with.


	6. Chapter 6

Back in the capital city of Gravity, Prince Gideon was starting to grow less and less patient. He sat in his throne, tapping his fingers against the arms of the chair that he was much too large for. A knock came at the door, somewhat quiet and nervous. "Come in..." He growled as he listened to the door squeak open and click shut. 

The King, Buck Gleeful, stepped forward, obviously nervous as he approached his son. "Gideon my boy?"

"Why are you here, instead of out there looking for that brat?" His voice lowered a bit as he asked his rage fueled questions. Buck let out a cough and looked around the dark room. "Now Son... I know I promised that I would find him but..."

"BUT WHAT!? OLD MAN!"

Buck swallowed a bit, patting the sweat from his cheeks as he nervously looked around the room. "But... we think that he may have escaped..."

Gideon stood completely still and silent, his face turning from red to purple as his anger grew. "ESCAPED!!?? What the hell do you mean he escaped!!???" He stood up, the fat around his neck appearing to move like gelatin as he began to scream at the king.

"Now son, we... we had every man in the country looking for him and nobody has seen him."  
"So father, how is it that he might have escaped?"  
"Well Son... some of the ships from the dock have gone missing so I suspect that he may have jumped onto one of them."

Gideon continued to glare at his father as he was told to just let the search go. His face turning from purple to its usual pale white. "Father... please tell me. Who was it that made you king?"  
"Well, I believe that was my father..."  
"Oh it was grandfather, was it? Was he the one who convinced you that you deserved more power? Was he the one who got you to poison his and your   
brother's drinks?"

"Well... no son... But I..."

"SILENCE!! Even if you have to search the corners of the earth I want that boy back, dead or alive. I had a deal with him and I'll be damned if he continues to make a fool of me like this!!"  
"Y...Yes, son... I'll... I'll send the marines out to search for him"

As the king began to leave the room there was a low rumbling of thunder, followed by a flash of lightning. "Better do it quickly, looks like a storm is brewing." 

O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.

Back on the ship, Dipper sat in the room with his ear pressed to the door. A frown spreading across his face as he heard everyone go into a frenzy. The sound of the storm growing louder and louder. He hated this, he hated the fact that not only was he to become the captains' sex toy. He also hated the fact that he was expected to idly sit by and do nothing while the ship was erupting in chaos.

"Stupid Bill... he can't tell me what to do." The young man frowned as he opened the door, his eyes going wide at the sight that greeted him. He had read stories, however, they were nothing like experiencing a real storm at sea. The sky was dark and churning. Clouds forming funnels as the winds blew the precipitation in all directions. The water from the ocean crashing in large waves up the sides of the ship. Occasionally making a wave so large that it would fill the deck with water and fish.

"No... no way...." The brunette whispered to himself in awe as he walked out to the deck. His eyes scanning about for the captain's shimmering gold jewelry or blonde hair. 

Bill stood behind the wheel, having shed his jewelry in favor of better control of the steering. He let out a loud groan as he twisted the wheel in order to navigate through the storm. The waves sweeping against the ship, as they nearly knocked him from his spot. 

The blonde glared at the sky as he shouted orders at his crew. His normally relaxed sense of self now replaced with someone much more serious. "PULL DOWN THE SAILS! BATTEN DOWN THE HATCHES!! DO A HEAD COUNT! THIS IS ONE HELL OF A STORM, WE CAN'T LOSE ANYONE!!"

Dipper stared at the other, admittedly impressed by his strong leadership skills. Then remembered that he was here to give him a piece of his mind. He ran up to the wheel and stood for a minute as though he were trying to collect himself. The blonde looked back to Dipper and glared. "Get back in the cabin now."

"No! I'm not some toy that you can just abandon."  
"GET YOUR ASS BACK IN THE CAB--"

In the middle of his sentence, a large wave knocked both of them into the raging waters of the ocean. Dipper, being a good swimmer began to swim around, desperately searching for the ship. That's when he noticed that he didn't see Bill. A wave of worry washed over the boy. Sure the captain was a horrible guy, but he would never wish for him to die. He listened for a moment as the crew mates gathered around the edge of the ship. Looking into the water as they cried out "Captain! Captain!"

He l listened as the crew members desperately cried out for the man who fell into the water, and looked around worriedly. Could it have been possible that the fearful demon of the seas, William Alexander Cipher... couldn't swim? He hated this, however, he hated letting another man die due to his negligence even more. Dipper sucked in a deep breath and dove down into the ocean. He wasn't sure if where Bill was, as the saltiness of the water stung his eyes. With his vision blurred he looked desperately until he spotted a humanoid figure, struggling to surface. His eyes, ears, and nose in pain he quickly swam over to the man and grabbed his hand. He swam upwards back into the stormy waves of the unforgiving sea and looked up at the ship. 

Bill clung onto Dipper, hacking and coughing as he tried to empty his stomach of the copious amounts of ocean water he had swallowed. Dipper was amazed that such a powerful man had this sort of weakness, and it seemed that everyone on the ship knew about it and yet nobody questioned Bill's authority. A rope eventually appeared by their side and without hesitation he wrapped it around Bill. As they pulled the captain up Dipper clung to the man tightly, who in turn clung onto him. �  
As they were pulled onto the ship Dipper couldn't help but notice as they were both carried back to the captain's room. His body went limp, and he knew that he would be in for a terrible punishment when the other woke up. The men threw Dipper onto the bed, then placed Bill on top of him. Some of them letting out snorts of laughter as they slowly left the two alone. Yes, Dipper was going to be in for hell when the captain woke up.

O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O

The next morning as Dipper awoke a strange thing happened. Nothing.

Absolutely nothing, the ship was quiet, and the captain... whom he would have assumed would have been taking the time to pleasure himself with the teen's body simply sat in his office, going through old charts and maps. Dipper stood up, staring in bewilderment at what was going on. Did the fearful captain suffer from a brain injury of some sort during his drowning? Dipper, being one to follow curiosity tried to make his way to the desk, only to be stopped by a slight choking sensation. 

He looked down, his pale skin being marred by what appeared to be a collar and chain, which kept him attached to the bed. He gave the heavy chain a few tugs, unsure as to how he hadn't noticed it before trying to walk off. Dipper stared at the pirate captain, wanting to get his attention. But then remembered what had happened the previous night. Surely, if he hadn't distracted him, they would not have nearly drowned. 

Bill continued to work, humming to himself, and on occasion singing a twisted song that he seemed to be pulling out of the dark recesses of his mind. His grin, spread wide across his face, almost as if he was unaware of what had happened the night before. Dipper listened outside to what was going on outside. Men were working, as usual, some of them tossing the bodies of those who had perished into the ocean. Erasing all memory of the storm that previous night. 

"Does... being a pirate mean you must always move forward no matter what?"

Bill stopped his work and set down the papers before getting up and walking over to the boy. "I'm surprised, most people would demand I take the leash off of them. By the way, if that was going to be your next question the answer is no, Pine Slut."

He took a moment to think of the boys' question and with a sigh gave a nod. "If we don't move forward then none of us will get what we truly want."

"But what about the ones who perished?"

"They did not die in vain. Life on the ocean itself is do or die. However, on my ship, it's do and die. Those who died were most likely the ones working the hardest." He sat down on the bed and tugged the chain in a passive manner to get the boys attention. "Come here." Dipper froze in terror at the sound of his command. His legs buckling together as he tried to crawl away, only to have the heavy chain stop him in his tracks.

Bill looked down at the terrified boy and grinned, his finely pointed teeth shining as though they were the tips of knives. Tears began to collect in the other's eyes, he had no idea what he was to expect. However he couldn't run away, Bill wasn't going to let that be an option. With a defeated whimper he stood up and walked to the other, whom, in some sort of sadistic trance appeared to be welcoming him by spreading his arms out wide.

Bill smiled as Dipper came to him, pulling the boy into his lap with a soft grunt. Dipper froze, his body stiffening a bit as he was pulled into the captains' lap. He hated this, he hated everything about this. Just thinking about what was going to happen to him made him want to throw up. A hand going up the back of his shirt and gently stroking him. He could feel the goosebumps rising, his breath hitching a bit as he felt the man's fingernails digging into his skin.

'Oh god... oh god oh god.......' He thought to himself as he felt the hands going lower and lower until they stopped to rest at his hips.   
"You look quite pathetic Pine Tree."


	7. Chapter 7

**Summary for the Chapter:**

> Trigger warning: Rape! Read at your own discretion!

**Notes for the Chapter:**

> I've always had difficulty writing about sex. I'm not sure why but it's always been hard for me to write about.

TRIGGER WARNING: RAPE  
READ AT YOUR OWN RISK.

Dipper let out a cry, his body trembling as he tried to pull away from the man. Only to have the chain he was wearing be yanked forward. Tears rolling down his cheeks as he coughed and sputtered. He glared at the captain who appeared to be doing whatever he pleased, his body, unfortunately, reacting to the light caresses that the man gave to him. "Please... please no..."

Bill couldn't help but to laugh, the once strong spirited Pine Tree, was beginning to succumb to what could be considered the least invasive touches one could muster. It made him want to see the boy writhing underneath him. It made him want to see him screaming his lungs out as he was slowly penetrated. He wanted to effectively mark this boy as his in order to make Prince Gideon unable to do so.

His hands pulled away from the body, a wide smirk on his face as he saw the delectable look of relief spread across Dipper's face. Oh, how he loved to torment him like this. His fingers danced in the air for a moment, then grabbed the front of the younger man's shirt.

Dipper's eyes went wide as he was pulled forward by the fabric of his clothing. A sickening rip could be heard echoing throughout the room as his pale skin was exposed to the other. "Please... you... you can't do this! You ca-" As he tried to reason with the insane captain Dipper found himself with a wad of the torn fabric being stuffed into his mouth. His body struggling to breathe as he choked on the invasive object. 

"Good boy, nice and quiet," Bill smirked and gently wiped the tears from his eyes. A soft laugh escaping from his throat as he pinned Dipper onto the bed. He wasted no time, studying the terrified look on the boy's face before dragging his mouth towards his neck. His tongue pressing and massaging itself against the boys adam's apple. 

Dipper let out a choked cry as the gag slid further into his mouth. Bill's tongue licked and massaged against his throat, tears rolling down his cheeks as he felt the other's teeth sinking into his skin. The brunette choked out a pained gasp as he felt the others teeth digging deeper and deeper into his throat, breaking the sensitive skin as he let out a cry. His body trembling, his eyes and mouth wide open as no sound came out of them. 

Bill smiled and pulled away just as he felt drops of blood run down the boy's neck. "Very good, maybe after we're done I'll give you a little treat." He reached up, wiping Dipper's tears away, laughing a bit as he saw him recoil once more. "What's the matter Pine Slut? Are you scared of me? Do you want to go back to Prince Gideon?"

Dipper froze completely and stared at Bill. Were his choices really to give in and let him have his way, or go back to that horrible monster? He looked up to the other, his body trembling, lips quivering, tears rolling down his cheeks as he bit his tongue and laid back on the bed. Anything, even dealing with this, would be 100.... no. A million times better than dealing with that obsessed prince.

Bill couldn't help but laugh at the pathetic sight before him. Never in his life had he seen anyone willing to sacrifice their masculinity in favor of everything else he could have. "That's a good boy, now let me do as I wish and perhaps I'll reward you later." 

He forced Dipper's legs apart, laughing a bit as he felt his pathetic attempt to close them once again. The brunette let out a whimper, staring wide eyed at the girth which pressed against his unprepared entrance. The breath from his nose came out in short gasps as the fear and adrenaline rushed through his body. 

"Hmmm.... do I use a sort of lubricant to make this easier for both of us?" Dipper nodded vigorously at the suggestion, tears rolling down his cheeks as he thought of the relief that would bring the situation. "Or.... do I just shove myself inside so that I can hear your pretty voice scream through that gag?"�  
The blonde grinned at him, his hips continuously pressing against the others hole. "Hmmm.... eenie.... meenie.... miney...." He grinned from ear to ear, the sadistic look in his eyes more than enough to make Dipper's blood run cold as he rammed himself into the brunette's unprepared entrance. 

Dipper tried to scream, however, the pain was so much that he couldn't even manage to emit a sound. Tears rolling down his cheeks as he felt the man ram into him. Blood trickling from his now ruined anus onto the sheets of the bed. Bill couldn't help but laugh, the pirate captain thrusting in whatever way he wished. Fast, slow, it didn't matter to him as long as it felt good.

"Incredible Pine-slut." He let out a laugh as he raised the brunette's legs, staring as the blood surrounding his cock acted as a lubricant. "With the way you feel around me, I could swear that your body was made for me to play with. There's no way in hell that I'm going to let that Gleeful kid take away such a great resource. He should have done you when he had the chance."

Dipper let out a whimper, his body numbing itself to the horrible pain it was in as his body fell limp against the bed. He couldn't move, he couldn't cry, all he could do was let Bill have his way and hope that it would be over soon. The bed frame squeaking and groaning as each thrust into his body caused it to violently scoot forward. Slamming into the wall with a rhythmic series of thuds. 

Dipper's voice moaned softly behind the bag, his drool pooling out of the corners of his mouth in copious amounts. He wanted this to stop, he wanted Bill to finish up. "You seem like you want something Pine Slut, and don't worry I'll give it to you."

The brunette looked up to the other, a dazed look in his eyes as he watched the other slowly change their positions. Without even pulling out he managed to stand up whilst forcing Dipper's hips into the air. "This way... everything will stay inside, and everyone will know who you REALLY belong to."

Dipper's eyes went wide as he immediately realized what the other was talking about. However, before he could even make the attempt to protest he felt it. Bill's member driving itself into his deepest parts. His body trembling at the others violent assault. The thrusts continued, so violent and strong that Dipper could feel one of the boards which supported the mattress break, then another one. The bed making a small dip beneath where their two bodies connected.

It happened quickly. Bill stopped with a moan as he made sure to thrust back into Dipper's deepest part. His seed flooding the crevices in the boy's body before he finally pulled out. "I can't wait to do that again with you Pine Slut." He let out a laugh as he began to get himself dressed. 

Tear's rolled down the boys cheeks as he watched the other, the man's essence dripping out of his body as he let out a sob. His thin body trembling in pain as he watched the other finish getting dressed as though he had just done something normal. Before closing the door and leaving his victim, alone, and in the dark.


	8. Chapter 8

**Summary for the Chapter:**

> Bill shows more of his merciless violent nature.

Bill slowly climbed off of Dipper, a look of satisfaction on his face as he stared into the blank eyes that adorned the red, pain filled face. He loved it, he loved the fact that he had broken the boy, and he loved the fact that he had beaten the loathful Prince Gideon. 

"I must say, kid, you're quite good..... so good in fact that I'm willing to make a deal with you." Dipper's only response to his proposition was a sob a some of the others semen slowly poured out of him. He couldn't move, he couldn't speak. All he could do was wait and listen. 

"First things first, you will be my servant. More than a cabin boy mind you because rather than care for the ship, you will care for me. You will dress the way I tell you to, eat when I tell you to tell. If I ask you to jump, you ask how high. Do you understand?"

"Ahhh.... uh...." Dipper's mouth tried to form words but all that came out were soft sounds mixed with light sobs. Almost like the babbling of an infant. "In return, I offer my protection from my crew and the rest of the world. As well, as money and supplies to be sent to your precious caravan. You do the job well, we will find a way to rendezvous with your family and I will supply them with a year's worth of supplies."

Dipper's eyes went wide at the sound of the deal. All he had to do was sacrifice himself, and his family would be taken care of. He whimpered and looked to the side. There was also the promise he made with Ford. If he took Bill's deal, then the majority of his family would be taken care of, however, if he didn't then who knows what Bill would do to him.

"So do we...." A fierce series of knocks ravaged the door, the blonde pirate glaring towards it as he slowly climbed off of the boy. "Oh, captain!" The shrill feminine voice sounded from the other side of the door. Bill opened it, and before another word could be stated a tall woman who seemed to be the essence of both the color pink and romantic passion walked into the room. "Oh, Bill someone said that they happened to walk by and heard that new kid screaming, so I thought that I'd see what that was......" Her eyes went wide as she found herself staring at the brunette, watching his legs buckle and twist on the bed as he tried to hide without the help of a blanket. 

"Pyronica, I'm rather busy right now.... besides? Have you forgotten the rules?" The atmosphere began to grow heavy, Bill's golden eye appearing to glow a soft blue color as he folded his arms across his chest. Pyronica began to stammer, her hands fidgeting nervously as she tried to explain herself.

On Bill's ship, there were only 3 rules. The Captain makes all the decisions, the captain gets all bragging rights, and nobody, under any circumstance is allowed in the Captain's room unless he placed them there himself. "Well Pyronica, you know the rules... hmmm... how should I punish you? Should I nail you to the front of the ship, let the rust of the metal and the salty sea air seep into your wound as the punishment sets in."

Tears began to roll down the woman's cheeks as she shook her head, silently begging for mercy from the man. "Or perhaps I should bind and gag you while all the other members have a go at you perhaps that would teach you to not be such a perverted wench.... Hmmmmm..... what do you think Pine Slut?"

All Dipper could manage was a soft whimper, tears rolling down his cheeks as he tried to drown out the conversation the two were having. "Oh, you say that she should go through both punishment ideas?" Pyronica looked up to him, practically screaming as she begged him for forgiveness. "I like the way you think! Teeth! Xanthar!" 

The two men ran up to the door, their vision of Dipper blocked by the sobbing Pyronica and Bill blocking the vision of the bed. "Yes, Captain!"

"Pyronica has forgotten not one, but two of my rules. As punishment, she will be spending the rest of the day nailed to the bow of the ship. Tonight, let's just say that the crew will be having a lot of fun. Now get her out there!"

"Yes, Captain!" The two picked up the woman, who had now gone limp from horror. She could have easily fought back against the two dragging her away, however, if she did try to resist the punishment Bill would give her would be much worse than anything she would go through that day.

Dipper listened in horror, the sound of her feet dragging along the wooden surface of the ship. Growing fainter and fainter until it stopped. One minute slowly turned into two. His heart pounding wildly as tears began to roll down his cheeks. What was only 5 minutes felt like 5 hours, then he heard it. The blood-curdling shriek that clearly filled the air like the violent, unrhythmic ringing of a thousand brass bells. 

"Please... please stop it.... Please!! Please no!!!!" Dipper began to scream and beg, his voice once found again as he began to thrash against the bed, the broken frame splintering from the force he used to try and escape from the nightmare he was in. Bill looked over at him, a soft laugh escaping his throat as he grabbed a handful of the boy's hair and lifted his head up. "How about this kid? If you don't agree to be my personal slave your beloved sister will go through shit much worse than that bitch Pyronica. Now I'll ask you again. Do. We. Have. A. Deal?"

Tears rolled down the boys cheeks, he hated himself, however, his promise to Ford meant nothing in comparison to keeping his twin safe. Without making a sound he gave a nod. "Good Boy."


	9. Chapter 9

Gideon sat in his office, his fat fingers drumming impatiently across the marble finish of his desk. He had sent all of his best men after Dipper, and yet there was no word on the boy or his whereabouts. It was almost as if everyone were making fun of him. It was as if his men were not finding him on purpose. Laughing at him. Mocking his rules and ideologies. "As soon as I see that boy I'm going to teach him a lesson he will never forget... mark my words.... he will be trembling underneath me, screaming at the top of his lungs for forgiveness..... I'll make it a public show for ever---" 

His thoughts were interrupted by a series of loud knocks, followed by his father running into the room. "Gideon my boy! I have good news.... and I have bad news for you my son! The good news is that they found Mason!" Gideon seemed to perk up a bit at the bit of news, only for his excitement to quickly waver away as he took a deep breath. "What's the bad news old man?"

"Well.... he's on a ship....."  
".... Who's ship?"  
"Well... it's a pirate's vessel and the captain is very well known...."  
"OH FOR THE LOVE OF CHRIST WHO THE HELL HAS HIM!!?"  
"Bill Cipher."

Gideon froze, a soft laugh emitting from his throat as he leaned back in his chair. "Father... I thought that we were past the age of telling cruel jokes.... I thought that we were more mature than that."

"Son.... I... I fear that this is no joke...."

"You expect me.... Gideon Gleeful... Prince of the Gravity Kingdom... to actually believe that his bride, is in the clutches of Bill Cipher... still, through some miracle.... actually living?"

"Son... he is on the same ship as Bill Cipher..."

A long pause came from the younger man, a dark scowl covering his face as he slammed his fists into his desk. "Prepare a ship with the best crew we can find... WE SET SAIL TOMORROW!"

O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O.O

Dipper let out a whimper as he slowly moved around the ship. Ever since he agreed to become Bill's personal assistant, it seemed to be non stop jobs and favors. All of which were given depending on the mood that he was in. Most of the jobs were fairly normal, clean the floors, organize papers, wash the captains clothing. Anything that could easily be done without worry. 

Then there were jobs which anyone would dread. The jobs in which Bill seemed to take the most pleasure in. Using Dipper's entire being to pleasure himself to the point of breaking the boy. Nights usually went without sleep, his body seemingly unable to move for days after the activities. "Dipper!" Stanford called out to the young man as he had just started to fall asleep.

The brunette let out a whimper as he slowly looked over to his uncle. He was so tired at that moment he couldn't even stand up straight. But he had to keep his deal with the captain a secret. "Dipper my boy are you feeling seasick again? Well, this will help you get over it, we're docking in 3 days. You and I will be able to escape this place." 

Escape. The word made Dipper want to scream. His body tensed a bit as he tried to hide his pain. Escape was no longer an option for him and he couldn't tell the man. "Th.... that's great.... I...." He froze as he felt a familiar hand on his shoulder. The long, tanned fingers gently drumming over his thin shoulder. "Ah... I see that you two have gotten close." The blonde leaned down, one of his longer necklaces draping over Dipper's shoulders and chest, adding, even more, weight to this already stressful situation. "I apologize for cutting your conversation short Sixer, but I need to speak to Pinetree here." He gripped Dipper's shoulder tightly, causing a soft yelp to escape from the younger man's lips. "In private."

Ford felt uncomfortable leaving his nephew alone with the sadistic man, however, he knew that it was safer for both of them to do as he said. The elder man watched as Bill dragged his nephew towards his cabin.

O.O.O.O.O.O.O.O.O.O.O.O

Bill grinned at Dipper, his sharp canine-like teeth gleaming in the soft candlelight which lit the cabin. "Pine Tree.... tell me... how long were you planning out your escape?" His long fingers wrapped around Dipper's throat with a vice-like grip. A low laugh escaping his throat as he watched the boy's face begin to turn red from lack of oxygen. "I....I...." The younger one tried to speak, however, without his much-needed air, he couldn't get the words out.

Bill continued watching, squeezing around the boy's throat as a series of laughs left his throat. Oh, humans were so much fun, especially how they could turn into a myriad of different colors. Green from illness, red from embarrassment, and even blue and purple from lack of oxygen. He continued to squeeze, watching as his face went from red to blue, and finally a dark purple before releasing him.

Dipper let out a series of choked sobs, sucking in as much air as he possibly could as tears rolled down his cheeks. "I...I'm sorry... I... it was my idea... I was planning it out before our deal, I just haven't had the heart to tell him it was off... please... I wasn't going to escape anymore..."

"Prove it Pine Slut." He opened the door and looked over to one of his crewmembers. "Get me, Stanford... now." They gave a nod and began to run towards the other side of the ship, dragging the elderly man towards the cabin. "Alright Cipher, what do you want with me you've already tortured that poor boy e..." Stanford froze, his eyes going wide at the sight of Dipper.

The paleness of his form, the tear-stained face, and of course the bruises on his neck, perfectly forming the shape of a hand. "Pine tree has something to say to you Sixer, go ahead, tell him."

"I....I.... The plan is off.... I.... I made a deal with Bill in order to keep my sister safe from harm.... I'm sorry..." Stanford's eyes went wide at the confession, he wasn't sure if he was angry with his nephew or felt sorry for him. Bill had used his weakness in a way that was cruel and sickening even for him. "Dipper... I..." He froze at the feeling of Bill's hand on his shoulder, his heart pounding wildly as he looked over to him. "Now.... how do I punish you Sixer?"

**Notes for the Chapter:**

> Sorry this chapter isn't as long as many of you would like. (and that it took me so long to get it out) I've barely been home for literally the past month. It's hard to write when you're home for maybe... two hours at the most before going to bed. Anyways I hope you enjoy.


End file.
